N,N′-二(2-羟苄基)取代咪唑烷的合成、表征及抑菌活性  

Synthesis,Characterization and Antibacterial Activity of N,N′-Bis(2-hydroxybenzyl) Substituted Imidazolidine Derivatives

作　　者：张明[1] 卢俊瑞[1] 辛春伟[1] 刘芳[1] 高蕙涵[1] 鲍秀荣[1] 陈丽然[1] 

机构地区：[1]天津理工大学化学化工学院,天津300384

出　　处：《应用化学》2009年第11期1282-1286,共5页Chinese Journal of Applied Chemistry

基　　金：国家自然科学基金(20576103);天津市高校科技发展基金重点(2006ZD33)资助项目

摘　　要：利用生物活性叠加原理,将"邻羟苯基"和"咪唑烷"分子片断有机结合,以水杨醛和乙二胺为起始原料,经缩合、NaBH4还原制得N,N′-二邻羟苄基乙二胺(2),进而与芳醛类化合物缩合关环,合成了8种N,N′-二(2-羟苄基)取代咪唑烷类化合物(3a^3h)。化合物的结构经1H NMR、IR、MS和元素分析等测试技术进行了表征。结果表明,水杨醛与乙二胺的缩合反应,可专一性地生成对称双缩席夫碱化合物(1);芳醛上的取代基对缩合关环反应有显著影响,邻、对位吸电基可使芳醛的羰基活化,有利于缩合关环反应的进行,邻、对位供电基可使芳醛的羰基钝化,不利于缩合关环反应进行。抑菌测试结果表明,质量分数为0.1%时,N,N′-二(2-羟苄基)取代咪唑烷化合物对不同菌株的抑菌活性具有明显的特异性,对白色念珠菌、大肠杆菌的抑菌率达100%。A series of N,N′-bis（2-hydroxy benzyl） substituted imidazolidine derivatives（3a～3h） were designd and synthesized by means of combining segments o-hydroxy phenyl and imidazolidine compounds,according to the reinforcement of biological activities.The N,N′-bis-o-hydroxy benzyl diaminoethane（2） was synthesized using salicylaldehyde and 1,2-diaminoethane,through condensation reaction and then reduction by NaBH4,and further cyclization with aromatic aldehydes.The structures of all the compounds were confirmed by ^1H NMR,IR,mass spectra and elemental analysis.The results show that the reaction of salicylaldehyde with 1,2-diaminoethane only formed the symmetric Schiff base（1）,the condensation of aromatic aldehyde with compound 2 was noticeably different for different substituents： o-,p-substituted electron-withdrawing groups can activate aromatic aldehyde and result in a higher yield of ring closing reaction,but o-,p-substitute electron-donating groups have opposite effects.The result of preliminary bioassay shows that the target compounds had obvious specificity to different bacteria at 0.1%（mass concentration）,and had an inhibitory rate of 100% on Monilia albican and Escherichia coli.

关 键 词：N N′-二(羟苄基)取代咪唑烷 合成 表征 抑菌活性 

分 类 号：O626.2[理学—有机化学]